Chemistry of Heterocyclic Compounds

, Volume 52, Issue 8, pp 555–558 | Cite as

Synthesis and cytotoxicity of aminomethylselenopheno[3,2-b]thiophene sulfonamides

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The reaction of 5-[(aminomethyl)ethynyl]thiophene-2-sulfonamides with in situ generated selenium(IV) chloride was used to synthesize 5-aminomethyl-substituted 6-chloroselenopheno[3,2-b]thiophene-2-sulfonamides. The cytotoxicity of these compounds was studied against HT-1080 (human fibrosarcoma), MH-22A (mouse hepatoma), CCL-8 (mouse sarcoma), MES-SA (human uterine sarcoma), MCF-7 (estrogen receptor-positive human breast adenocarcinoma) cell lines, as well as the normal NIH 3T3 cell line (mouse fibroblasts).

Keywords

selenium selenophene sulfonamide thiophene cytotoxicity electrophilic addition intramolecular cyclization 
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Notes

This work received financial support from the Latvian Council of Science (grant No. 2012/447).

References

  1. 1.
    Drake, N. Selenium: Are You Getting Enough to Reduce Your Risk of Cancer? iUniverse.com: Lincoln, 2001.Google Scholar
  2. 2.
    Selenium: Its Molecular Biology and Role in Human Health, 3rd ed.; Hartfield, D. L.; Berry, M. J.; Gladyshev, V. N., Eds.; Springer: New York, 2012.Google Scholar
  3. 3.
    Arsenyan, P.; Rubina, K.; Shestakova, I.; Domracheva, I. Eur. J. Med. Chem. 2007, 42, 635.CrossRefGoogle Scholar
  4. 4.
    Shahabuddin, M. S.; Nambiar, M.; Choudhary, B.; Advirao, G. M.; Raghavan, S. C. Invest. New Drugs 2010, 28, 35.CrossRefGoogle Scholar
  5. 5.
    Arsenyan, P.; Shestakova, I.; Rubina, K.; Domracheva, I.; Nesterova, A.; Vosele, K.; Pudova, O.; Lukevics, E. Eur. J. Pharmacol. 2003, 465, 229.CrossRefGoogle Scholar
  6. 6.
    Arsenyan, P.; Paegle, E.; Belyakov, S.; Shestakova, I.; Jaschenko, E.; Domracheva, I.; Popelis, J. Eur. J. Med. Chem. 2011, 46, 3434.CrossRefGoogle Scholar
  7. 7.
    Vasiljeva, J.; Domracheva, I.; Arsenyan, P. Tetrahedron Lett. 2016, 57, 196.CrossRefGoogle Scholar
  8. 8.
    Arsenyan, P.; Vasiljeva, J.; Shestakova, I.; Domracheva, I.; Jaschenko, E.; Romanchikova, N.; Leonchiks, A.; Rudevica, Z.; Belyakov, S. C. R. Chim. 2015, 18, 399.CrossRefGoogle Scholar
  9. 9.
    Mortikov, V. Y.; Litvinov, V. P.; Shestopalov, A. M.; Sharanin, Yu. A.; Apenova, E. E.; Galegov, G. A.; Abdullaev, I. I.; Asadullaev, T. B.; Abdullaev, F. I. Pharm. Chem. J. 1991, 25, 312. [Khim.-Farm. Zh. 1991, (5), 41.]Google Scholar
  10. 10.
    El-Bahaie, S.; Assy, M. G.; Hassanien, M. M. Pharmazie 1990, 45, 791.Google Scholar
  11. 11.
    Hwu, J. R.; Lai, L.-L.; Hakimelahi, G. H.; Davari, H. Helv. Chim. Acta 1994, 77, 1037.CrossRefGoogle Scholar
  12. 12.
    Méplan, C.; Hesketh, J. Cancer Treat. Res. 2014, 159, 145.CrossRefGoogle Scholar
  13. 13.
    Socha, K.; Kochanowicz, J.; Karpińska, E.; Soroczyńska, J.; Jakoniuk, M.; Mariak, Z.; Borawska, M. H. Nutr. J. 2014, 18, 13.Google Scholar
  14. 14.
    Batist, G.; Katki, A. G.; Klecker, R. W., Jr.; Myers, C. E. Cancer Res. 1986, 46, 5482.Google Scholar
  15. 15.
    Potapov, V. A.; Musalov, M. V.; Musalova, M. V.; Amosova, S. V. Curr. Org. Chem. 2016, 20, 136.CrossRefGoogle Scholar
  16. 16.
    Potapov, V. A.; Amosova, S. V. Russ. J. Org. Chem. 2003, 39, 1373. [Zh. Org. Khim. 2003, 39, 1449.]Google Scholar
  17. 17.
    Potapov, V. A.; Musalov, M. V.; Abramova, E. V.; Musalova, M. V.; Rusakov, Yu. Yu.; Amosova, S. V. Chem. Heterocycl. Compd. 2014, 49, 1821. [Khim. Geterotsikl. Soedin. 2013, 1965.]Google Scholar
  18. 18.
    Amosova, S. V.; Martynov, A. V. Mini-Rev. Org. Chem. 2010, 7, 23.Google Scholar
  19. 19.
    Ninomiya, M.; Garud, D. R.; Koketsu, M. Coord. Chem. Rev. 2011, 255, 2968.CrossRefGoogle Scholar
  20. 20.
    Ling, C.; Zheng, Z.; Jiang, X. C.; Zhong, W.; Li, S. Bioorg. Med. Chem. Lett. 2010, 20, 5123.CrossRefGoogle Scholar
  21. 21.
    Soriano-García, M. Curr. Med. Chem. 2004, 11, 1657.CrossRefGoogle Scholar
  22. 22.
    Guo, X.; Baumgarten, M.; Müllen, K. Prog. Polym. Sci. 2013, 38, 1832.CrossRefGoogle Scholar
  23. 23.
    Arsenyan, P.; Oberte, K.; Pudova, O.; Lukevics, E. Chem. Heterocycl. Compd. 2002, 38, 1437. [Khim. Geterotsikl. Soedin. 2002, 1627.]Google Scholar
  24. 24.
    Lukevics, E.; Arsenyan, P.; Belyakov, S.; Pudova, O. Chem. Heterocycl. Compd. 2002, 38, 763. [Khim. Geterotsikl. Soedin. 2002, 867.]Google Scholar
  25. 25.
    Chen, H.-H.; May, J. A.; Lynch, V. M. J. Heterocycl. Chem. 1999, 36, 249.CrossRefGoogle Scholar
  26. 26.
    Prugh, J. D.; Hartman, G. D.; Mallorga, P. J.; McKeever, B. M.; Michelson, S. R.; Murcko, M. A.; Schwam, H.; Smith, R. L.; Sondey, J. M.; Springer, J. P.; Sugure, M. F. J. Med. Chem. 1991, 34, 1805.CrossRefGoogle Scholar
  27. 27.
    Arsenyan, P. Tetrahedron Lett. 2014, 55, 2527.CrossRefGoogle Scholar
  28. 28.
    Arsenyan, P.; Vasiljeva, J.; Belyakov, S.; Liepinsh, E.; Petrova, M. Eur. J. Org. Chem. 2015, 5842.Google Scholar
  29. 29.
    Report of the International Workshop on in vitro Methods for Assembling Acute Systemic Toxicity; NIH Publication No.: 01-4499, 12 (2001).Google Scholar

Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  1. 1.Latvian Institute of Organic SynthesisRigaLatvia

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